What is the first synthetic quinoline antibiotic?

Nalidixic acid 

Nalidixic acid is the first synthetic quinolone antibiotic. It  is  a white  to  slightly   yellow crystalline powder which is odorless. Nalidixic acid is insoluble in water. The melting point of  nalidixic acid is  445⁰F (NTP,1992) . It is strongly active against gram-negative bacteria but show minor activity against gram-positive  bacteria. The molecular weight of nalidixic  acid is 232.23 gm/mol. It is also known as, Uronidix,Innoxalon, Betaxina,Urisal, Nogram, Navigramon etc.

■Structure:-

The moleculer formula of nalidixic acid is, 

                                                          [C12H12N2O3].

The IUPAC name of nalidixic acid is, 1-ethyl-7-methyl-4-oxo-1,8-naphthyride-3-carboxilic acid.

■Synthesis:-

■Mechanism of action:-

The active metabolite of nalidixic acid, i.e., hydroxynalidixoc acid, strongly and reversibly binds to DNA and interferes with RNA and protien synthesis. 

■Uses:-

It is used in urinary tract infections caused by gram-negative microorganism including E.coli, Enterobacter species, Proteus species.

■Side-effects:-

The overdose of nalidixic acid shows several adverse effects, 

1. Rash.
2. Hives.
3. Itching.
4. Difficulty in breathing.
5. Tightness in chest.
6. Blurred vision.
7. Tingling sensetion.
8. Change in color vision.
9. Convulsion.

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